I'm doing something I'm not sure is legal--but is it permissible not to lift Hopelessness with your founder? I have an adult-start with a Pleasure sim founder and bad luck with jobs. She's female so she can have an heir without moving anyone in. I've just never seen it done before so I don't know if it's legal, but most people start in college...
Yes, it is legal. It will delay everything by a generation but you will have longer to skill up the child, and get them friends, thus improving their chances. You will also be stuck with a useless, senile elder on the lot eating food and taking up one of the places.
I have just completed the first stage of an adult start- unlocking hopelessness and adventure. I have played an adult start now about six or eight times. It relies on a high element of luck. This time I used a female knowledge sim. She took 5 days until adventurer came up. Adventurer or medical were my first two preferences for careers, so that was the first piece of luck. In the five days she made 8 friends by talking to almost every walkby. A game of snowball fight or water balloon gets them close to friends status, then talk-gossip or talk about hobby. I try to stop at about 60 -70 points as there is a greater chance of them visiting again. I also managed 5 body points, 4 mechanical and 2 charisma, so she could take advantage of promotions immediately.
Fortunately this time I didn't get any of the bad chance cards- I had a couple of games killed by them. If you get several demotions or fired there is not enough time left to get to the top of your career before senility sets in.
She reached the top of her career by day 27, chose the elixir as the career reward. Meanwhile she found a partner who is a GP. On the next Tuesday he moved in. This is as far as I have played. I am still trying to figure out a set of rules incorporating Free Time, as I don't think Pinstar is planning to update them.